


Rolling Through Town, No Strings Attached

by RachelAnarchy



Category: Supernatural
Genre: Dean x Reader, Dean x You - Freeform, Drabbles, F/M, Occasional fluff, Plot What Plot/Porn Without Plot, Smut, Supernatural - Freeform, one shots, some angst i guess
Language: English
Status: In-Progress
Published: 2015-10-27
Updated: 2016-01-11
Packaged: 2018-04-28 05:31:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,094
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5079664
Author URL: https://archiveofourown.org/users/RachelAnarchy/pseuds/RachelAnarchy
Summary: <blockquote class="userstuff">
              <p>You and Dean once had a fling when he worked a case in your city. Now he makes a point to swing by your neck of the woods whenever the boys drive through your state. Yeah, he's bad for you, but it's hard to turn him down since you're fully aware what those sexy lips of his are capable of.</p><p>Each "chapter" will be a smutty drabble/one shot in the reader's POV, detailing a hot as hell encounter with Dean Winchester. Unless I'm in a fluff kind of mood, that is.</p>
            </blockquote>





	1. Chapter 1

His hands were all over you the second your front door slammed shut.

Strong arms wrapped around your waist to pull you close before his fingers firmly gripped your ass, forcing the front of your body against the rigid cock straining to be released from his jeans. He kissed you fervently, greedily, like a parched man in the desert would consume a tall glass of water. And damned if you didn't match his intensity with everything you had.

It had been months since your first night with Dean Winchester, a marathon fucking session you figured would be the last you'd ever see of him. You knew his reputation from some other hunters you were familiar with, not to mention the Harvelle girls, may their souls rest in peace. But when Garth pointed the Winchester boys in your direction for your expertise with lore and Dean laid on the charm, you were pretty much done for.

Your hands traveled up his torso and you cursed every flannel and canvas layer keeping you from your goal. Grabbing either side of his jacket, you hurriedly peeled it over and off his broad shoulders to throw it to the floor. His mouth curved into a smile against yours as a response to your eagerness. In return, you gave him a quick shove as punishment. He hardly budged from your attempt; you could hold your own but you weren't a hunter. Research and mythology was your skill set, and besides, Dean was over six feet of hard muscle and you could think of much better things to do with that chiseled frame than spar with the man. With that thought, you pulled him back into your kiss.

Between heated kisses and roaming hands, the two of you lost your tops in the scuffle. Dean paused long enough to gaze appreciatively at the purple lace bra you had picked out for tonight, before reaching around to undo the clasp with expert hands. He hooked his arms around your thighs to lift you up, eliciting a surprised squeak from you at the sudden movement. Your nipples hardened when they rubbed against the bare skin of his chest and wetness pooled between your legs. He walked behind your couch in the center of the room, sitting you on top of the back. When you were more or less situated with your legs wrapped around his waist, he went to work on your breasts. Taking one peak in his mouth, he teased the sensitive tip with his tongue and just barely grazed his teeth over the delicate skin. You moaned softly when he grasped a handful of your hair to tilt your head back for better access. Once you were fully exposed he lavished his attention to your other breast and slid his free hand down to attend to the throbbing bundle of nerves at your center.

With his thumb, Dean rubbed your clit over your jeans in small circles, increasing pressure and speed and building you up all while he sucked and teased one nipple then the other. His unshaven face tickled you roughly, adding to the pleasure you felt nearly from head to toe. He smelled of leather and a trace of burning wood, mixed with a scent that was all his own. Your hand found the back of his neck to cradle it over shortly cropped hair and pulled him closer, encouraging him to continue working you over. You sought out his length with your other hand, dismayed to find he was still wearing his pants. A whimper escaped your lips. He looked up at you expectantly and you tugged at his belt. Raising a brow, Dean simply held your gaze and worked your pleasantly aching nub even faster.

Your orgasm built up deep inside, your whole body shaking when he took a nipple into his mouth once more. Nails raking over his back, you shouted his name as you came. It only took you a few seconds to come back down to reality and by then you wanted him inside you.

Now.

You leaned forward to undo his fly while he unbuckled his belt. His cock sprang up when freed from his jeans, allowing you to take the thick, silken shaft into your hand. Dean made a rough sound of pleasure as your fingers circled around him. He stepped toward you after assisting with the removal of your own pants and once the two of you were naked, skin to skin, you spent several seconds in each other’s arms. His head buried in the crook of your neck while he trailed his fingers up and down your spine. You rubbing him slowly as the tingling heat built back up in your pussy.

If you didn’t know him any better, you’d think Dean was stalling. That he was prolonging your night together to make the whole experience last longer, so he didn’t have to leave so soon and meet back up with his brother.

No, that couldn’t be it.

Could it?

You promptly dismissed any ideas of Dean as relationship material. This thing the two of you had going worked fine as it is. Quick fucks if and when your schedules allowed it. Best part was, no one got hurt. You were both adults and knew exactly what you were getting into. This was just about the sex.

But... The way he held onto you like he didn’t want to let you go left you unsure of exactly what to think. All you knew right now is you weren’t willing to end up with a broken heart.

Shifting slightly atop the back of the couch, you positioned yourself to press his erection along the length of your slit. Dean cursed and lifted his head to kiss you deeply. You returned the kiss passionately and rocked him against your wet heat. He brought his hand between the two of you to tease your slick entrance with the head of his cock. You squeezed your legs around him tighter and urged him forward. He obeyed, pushing into you with another vivid curse and satisfied groan. 

Him finally inside of you again, filling you up, was exquisite torture. You knew this night wouldn’t last. But damn it, you’d enjoy every last minute of it. Dean moved back and forth, slowly at first then building up speed. You moved your hips in sync with his, a sheen of sweat forming on both of you. The only noise breaking the silence were your moans and sound of skin feverishly meeting skin.

After a while could feel another orgasm starting and you quickened your pace. You held onto his shoulders tightly for support while he wrapped both arms around you in an iron grip. Dean sped up as well, and you threw your head back as you came, him following shortly after.

You remained locked in your embrace as you both caught your breath, his face once again nuzzled in the curve of your neck. Finally he let out a long sigh, a man utterly satiated and spent.

At that you smiled, and spoke the first bit of conversation of the night.

“It’s good to see you again too, Dean."


	2. Chapter 2

*******

It was late.

You and Dean and been burning the midnight oil at a local university's archives, a crisp $100 bill slipped to the campus security guard allowing after-hours access to their records. The case the Winchesters were working was actually a couple of towns over, but Dean had convinced his brother your knowledge of lore and legend would be well worth his detour here to meet up with you. 

He wasn't wrong. Though he had clear ulterior motives focused intently on getting you back in bed, your research broke the case wide open. You made a vital connection while digging up some 19th century news articles about the family who owned the mansion where some of their help recently turned up mauled to death, hearts missing. Sam had assumed this was a cut-and-dried bout of werewolf attacks, but you found the family's history to be even more complicated. 

Turns out they had lived in the area for generations, and different members owned several sizeable properties over the years throughout the tri-states, their ancestry dating back to the pre-civil war era. Around the time Lincoln delivered the Emancipation Proclamation, a few of their kin were reported missing and others showed up dead, having been murdered in a similar fashion to today's vics. 

That's when things got really strange. Folks in a nearby family known to be somewhat of an economic and land ownership rival of this one started ending up dead too. Exsanguinated, to be exact. One record after another followed this pattern: Someone in one family gets mauled, then someone in the other gets their blood drained. Every once in a blue moon they'd come across a decapitation. This gruesome tit for tat went on for decades, only fizzling out when the Great Depression brought some of America's richest families to their knees. 

You supposed their vendetta against each other was thrown to the wayside when their otherwise cushy lives were jeopardized as the country's GDP went down the toilet. 

“So,” Dean said, walking around his Impala to let you in the passenger seat. “We're dealing the Monster Mash version of a blood feud here. Like the Hatfields and McCoys.” 

“Yeah,” you agreed with humorless laugh. “But with fangs.” 

“Yep.” He shut the creaky door and strode over to the driver's side. Slipping in, he let out a grumbly sigh. “Lots of damn fangs. “

You fiddled with your hands in your lap. Dean and Sam were capable hunters, the best probably, but you still worried about them. However, from what you'd heard over the years, they'd seen a lot worse than some rival vamp and were clans. 

But it didn't matter. They were good people, and the world would be a little darker if they were gone. 

_Not if, but **when** they were gone,_ you silently corrected. That was the hunter's life and you best remind yourself of it. Dean, and Sam too, they'd never settle down into an apple pie existence. For them it would end bloody, and sooner than they'd think. Probably even sooner for Dean... 

His deep voice roused you from your grim thoughts. 

“Did you want to call it a night then?” 

“Hm? Uh, yeah. It's pretty late. You texted Sam with the new developments?” 

“Uh huh.” He turned the key and the engine roared to life. “He agreed that we'd pick up the hunt in the morning.” 

You nodded. “Back to my place?” 

Dean pulled out of the lot, tires squealing. Casting you a sideways glanced, he smiled. “Thought you'd never ask.” 

Sleek and black, the classic car cut through the night over an empty two-lane highway on the drive home. You shifted and crossed your legs. All that horsepower revving through the supple leather seats and having Dean less than an arm's length away brought your mind back to the here and now. And what happened to be on your mind at the moment was, well...

Dean pushed a cassette into the tape deck and hit _Play_. The sultry and relaxed blues-style guitar of Jimi Hendrix’s “Red House” filled the cabin. Your lips curved into a wicked smile but you kept your eyes focused on the road as you unbuckled your seatbelt. He glanced over to you at the sound and furrowed his brows.

“Hey.” His eyes flicked to the front then back to you. “What are you up to?”

You shrugged and scooted close to him on the bucket seat, sliding your hand over his thigh. Dean coughed a bit and sat up a little straighter. Resting your head on his shoulder, you continued to rub his inner thigh, slowly moving your way up his leg. Soon enough, his cock was straining against the denim fly. You brought your hand to his crotch, firmly massaging the swollen bulge. His eyes remained trained straight ahead but his breathing kicked up, his chest rising and falling slightly faster than before.

Still working his hard-on, you lifted your head and inched close enough to bring your mouth to his ear and lightly nibble the lobe. He breathed in sharply and you smiled with your lips against the shell of his ear. The first night the two of you slept together, you learned he reacted very well to licks and nips in certain places, and you planned to fully exploit that knowledge for as long as you had him this time around.

Kissing his neck, you snuck your hands under his shirt to undo his belt and then the button and zipper of his jeans. The muscles in his clenched jaw ticked as you pulled out his rock-hard erection and began stroking back and forth, adding extra pressure to the sensitive underside. His length throbbed under your touch and Dean bit and licked his lips as you teased a drop of precum around the head with your thumb. You continued your up and down movements, adding a light rotation at the top, nearly bringing him to the edge.

When it seemed he was getting close you stopped to move your hand down to cup and squeeze his balls. Dean groaned and the Impala’s engine rumbled even louder, his foot briefly pressing harder on the gas. Dipping your head down, you met his green eyes and smirked, rather enjoying the effect you had on him. He lifted his arm to allow you unfettered access and slow and steady, you took every inch of him in your mouth.

Dean swore a silent oath, twisting your hair once around his hand. Lips over your teeth and throat relaxed, you moved down his shaft all the way to the hilt. He urged you on gently as you wrapped your hand around his cock to assist in the sensations your mouth provided. You took your time, thoroughly enjoying the feel of him in your mouth and his taste on your tongue.

After a while, he started to thrust his hips just a bit to match your movements and his hand pulled and pushed your head with a touch more force. You added an extra move whenever you reached the top, allowing your tongue to twist around and press against the crown. At that, Dean’s grip on your hair tightened and you sensed he was trying very hard not to buck his pelvis up too much or too quickly. You only redoubled your efforts, taking him all the way in and teasing him with your hand and the tip of your tongue.

“I’m... I’m about to...” he rasped and you nodded, not taking your mouth off of him. Reaching your hand down, you massaged his sac and felt the pulses starting. Dean said your name on a shuddering breath and the first spurts of salty-sweet cum hit your tongue and you swallowed, sucking him off until he became too sensitive.

“Fuuuck,” he growled. You lifted your head after discreetly wiping your mouth and covering him back up. “That was... amazing.”

You were about to settle back into the passenger side when he pulled you to him for a quick but deep kiss. When you broke apart he smiled lazily, glancing in your direction from under hooded eyes.

“You know,” he began. “There’s something about having my taste on your tongue. It’s like I know, for the moment at least, I have you all to myself.”

Back and forth, you lightly traced your thumb over his full lower lip. “Is that so?”

He nodded in response and kissed the tip. You sat back with a smile and a deep sigh before checking out your window to see where you were at.

“Uh, Dean? My place is like _way_ back there.” You tipped your head in the direction opposite of where he was driving.

Dean Winchester simply smiled and checked his mirrors before pulling a U-turn on the quiet blacktop.


	3. Chapter 3

**Notes for the Chapter:**

> Fluff break!

*******

The two of you had every intention of keeping each other awake for a good part of the night, but after Dean stripped to his boxer briefs and you stepped into the restroom to freshen up, you emerged to find him sound asleep, sprawled out over your down comforter. You were pretty sure he'd be quite content to be nudged awake, especially since the only thing you still had on was a pair of panties, but you decided he needed the rest. As a rule, hunters don't get much sleep, but you'd been keeping him especially busy over the last couple of nights.

_Poor guy deserves a break,_ you mused with a smile. You pulled his t-shirt from where it landed on the back of your desk chair, all the while admiring Dean's long muscled lines. He lay on his stomach, one knee tucked up to the side and his arms wrapped around a pillow.

Absentmindedly, you pressed the well-worn cotton under your nose and couldn't help but notice how soft Dean Winchester looked at this moment. His usually tense frame was loose and relaxed, the worry lines on his face were smoothed, and his slight-yet-adorable tummy showed above the rumpled spread. He was completely vulnerable, trusting your company during some of his rare moments of rest.

One brow lifted slightly and his eye just barely opened. “What’re you up to?” Dean asked in a sleep-gruff voice.

You quickly spun and slipped his shirt over your head. “Nothin’. Scoot.”

“Mmph.” He protested briefly but gave you some space beside him. “Looks good on you,” he noted, eyeing the thin fabric over your naked curves.

“Well, don’t get any ideas. You need to get some sleep if you want to go after those vamp and were clans tomorrow.”

You nestled beside him; the bed was already warm from his body heat.

Dean groaned and pulled you closer, draping his arm over your waist protectively. “ _You_ don’t get any ideas.”

Rolling your eyes, you smiled at his mumbled retort. Dean’s comebacks tended to be a bit weak, but you had to admit they were kind of endearing. He curved against your back and his breathing steadied as he drifted off. You sighed and threaded your delicate fingers through the calloused ones resting on your midriff, trying to talk yourself out of the fact the two of you fit so well together. That you and Dean Winchester might have a shot at sharing an apple pie life.

Because the second you allowed yourself to believe that, you knew your heart was done for.


End file.
